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Military Guy is good for finding tunnels but if you just surround the edge of the map with a fence you already reduce the escapes. However in a big prisone it can be hard to find those tunnels that have been started long ago and then they break out. So he comes in very handy aswell.
the two females are by far the least useful as you don't need extra income or more suppressions. they are more for Role Playing. Extra money is nice for your very first prison but even then a couple of bucks per contraband is hardly worth it.
Some of the Overpowered ones like pacifier and The Lobbyist can help you if you having trouble dealing with Supermax and max prisoners. But honestly you shouldn't learn to play with them. The other ones are pretty specific. Only useful in one area. I tend to only pick them when I want to do something very specific.